This chapter lays out the first phase of my new argumentative approach to the problem of whiteness by developing a new account of wrongful benefiting grounded in the principle of fair play. Prominent accounts of wrongful benefiting construe gains as wrongful when sourced in some prior wrongdoing, or when their conferral involves some correlative harm to others. My fair play account goes further, showing how the non-voluntary provision of benefits can qualify as wrongful in itself, that is, independently of any occurrent harm to others or causal connection to prior wrongs or injustice. In particular, I argue that certain kinds of structurally conferred group-based benefits or privileges can ground obligations to relinquish specific gains for purposes of general redistribution wholly as a matter of social fairness, even when beneficiaries themselves are innocent of personal wrongdoing. This approach turns on a new conception of free-riding which eschews necessary appeal to beneficiaries’ mental states or volition, and which I therefore term externalist. Drawing on work by Iris Marion Young, I also argue that these obligations to relinquish are well-construed as falling under the domain of political responsibility, which I characterize along the way.